It's not uncommon for the hull to deck joint to leak. The fix is to remove the rub-rail, deck to hull fasteners, pry the deck and hull apart, clean or grind smooth, lay a bead of something like 3M 5200 and re-assemble. It's not a fun or easy job so make sure the water is coming from the deck to hull joint before starting.

I owned a Peason 26 for 10 years. The topsides are pretty high for that sized boat. I think you would have to be over 45 degrees or more before the rub rail would be in the water. If you do this regularly you are not sailing the boat very well.

Obviously, boats with more freeboard are going to bury the rail at greater angles of heel. However, saying that you would need to be "knocked down" to do it is a gross exaggeration! I recently crewed aboard a 50 year old, 53 foot Yawl in the Master Mariners Regatta. We probably dipped the rail on that old girl 3 times during the race, on a relatively mild, but gusty day. After all, on a boat with average freeboard, you don't have to be heeled over that far to have a wave bury the rail. In addition, any time you take water over the bow, the rails are going to get wet. Not trying to be argumentative or go off topic. I simply think we should avoid exaggeration, especially when addressing a self described newbie. IMO, the rail, hull/deck joint is certainly a candidate for causing the OP's leak.

yeah, I've never been healed more than 20 degrees with this boat. However with the choppiness in the waves we encounter in lake Huron I know that rub rail gets a lot of water hitting the underside of it. We have had some bad spots in the rubber section of the rail since we bought it and I will be replacing it this weekend. While I have it off I am going to take a few days and reseal that entire deck joint thoroughly. I will let everyone know what happens.

I do like the through hull suggestion as I do have 2 on the port side but none on the starboard. I will definitely make sure those are not playing a part in this.

I do like the through hull suggestion as I do have 2 on the port side but none on the starboard. I will definitely make sure those are not playing a part in this.

I have a check list I run through before I go out. I have someone read it to me as I go from bow to stern. Takes about a minute to run through. I got tired of being heeled over in a blow, looking into the salon and realizing I'd left a hatch open, not emptied the standing water in the head, left a sink drain open, etc. and had water in the salon. One time a guest had put together a great lunch, and unknowingly, placed it in the dry sink. On Port tack, the sink is much lower than the water line and I hadn't closed the valve. That was one soggy lunch!
Here is a copy of the list if you are interested. When you look at it, I think you will see how easy it is to forget something on it:

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